I'm thinking of throwing $15 his way just to see what comes out, and see if it sparks some new ideas for me -- i.e., I'm not paying him for a polished final design for my site, I'm paying him for his thoughts (in PDF form) on how my site might look different.

I might not like his idea, and it might just offer a contrast that helps me suss out what I like about my current design. But as it was only 15 bucks (not much invested from me OR him), I won't feel bad about just chucking the results.

If I were paying someone for a real site redesign, I would lay out a lot more than $15, but I would also expect to go through whatever steps necessary to come up with a finished product that I would actually use (because if I'm paying real money, it had better not be a waste).

In any case, I'm waiting until he has some example sites online... so I can tell if he's a talented designer doing rapid/rough work (useful to me), or a weak/inexperienced designer who is just making bad designs (in which case I'll pass...).